Research Article
Year 2022,
, 590 - 593, 27.12.2022
Abstract
References
- [1] Lekgau K., Raphoko L.A., Lebepe C.M., Mongokoana D.F., Leboho T.C., Matsebatlela T. M., ... & Nxumalo W., Design and Synthesis of 6-Amino-quinoxaline-alkynyl as Potential Aromatase (CYP19A1) Inhibitors, J. Mol. Struct., 1255 (2022) 132473.
- [2] Osmaniye D., Karaca Ş., Kurban B., Baysal M., Ahmad I., Patel H., ... Kaplancıklı Z. A., Design, synthesis, molecular docking and molecular dynamics studies of novel triazolothiadiazine derivatives containing furan or thiophene rings as anticancer agents, Bioorg. Chem., 122 (2022) 105709.
- [3] Sayyad N. B., Sabale P. M., Umare M. D., Bajaj K. K., (2022). Aromatase Inhibitors: Development and Current Perspectives, Indian J. Pharm. Educ. Res.56 (2022) 311-320.
- [4] Shah V., Bhaliya J., Patel G. M., In silico docking and ADME study of deketene curcumin derivatives (DKC) as an aromatase inhibitor or antagonist to the estrogen-alpha positive receptor (Erα+): potent application of breast cancer, Struct. Chem., 33 (2022) 571-600.
- [5] Rashdan H. R., Shehadi I. A., Triazoles Synthesis & Applications as Nonsteroidal Aromatase Inhibitors for Hormone-Dependent Breast Cancer Treatment, Heteroatom Chem., (2022).
- [6] Çevik U. A., Celik I., Mella J., Mellado M., Özkay Y., Kaplancıklı Z. A., Design, Synthesis, and Molecular Modeling Studies of a Novel Benzimidazole as an Aromatase Inhibitor, ACS omega. 7 (2022) 16152-16163.
- [7] Osmaniye D., Levent S., Sağlık B. N., Karaduman A. B., Özkay Y., Kaplancıklı Z. A., Novel imidazole derivatives as potential aromatase and monoamine oxidase-B inhibitors against breast cancer, New J. Chem., 46 (2022) 7442-7451.
- [8] Ammazzalorso A., Gallorini M., Fantacuzzi M., Gambacorta N., De Filippis B., Giampietro L., ... Amoroso R., Design, synthesis and biological evaluation of imidazole and triazole-based carbamates as novel aromatase inhibitors, Eur. J. Med. Chem., 211 (2021) 113115.
- [9] Acar Çevik U., Celik I., Işık A., Ahmad I., Patel H., Özkay Y., & Kaplancıklı Z. A., Design, synthesis, molecular modeling, DFT, ADME and biological evaluation studies of some new 1,3,4-oxadiazole linked benzimidazoles as anticancer agents and aromatase inhibitors, J. Biomol. Struct. Dyn., (2022) 1.
- [10] Ana G., Kelly P. M., Malebari A. M., Noorani S., Nathwani S. M., Twamley B., ... Meegan, M. J., Synthesis and Biological Evaluation of 1 (Diarylmethyl) 1H 1, 2, 4 Triazoles and 1 (Diarylmethyl) 1H Imidazoles as a Novel Class of Anti-Mitotic Agent for Activity in Breast Cancer, Pharma., 14 (2021) 169.
- [11] Asadi P., Khodarahmi G., Farrokhpour H., Hassanzadeh F., Saghaei L., Quantum mechanical/molecular mechanical and docking study of the novel analogues based on hybridization of common pharmacophores as potential anti-breast cancer agents, Res. Pharm. Sci., 12 (2017) 233.
- [12] Mojaddami A., Sakhteman A., Fereidoonnezhad M., Faghih Z., Najdian A., Khabnadideh S., ... Rezaei Z. Binding mode of triazole derivatives as aromatase inhibitors based on docking, protein ligand interaction fingerprinting, and molecular dynamics simulation studies, Res. Pharm. Sci., 12 (2017) 21.
- [13] Song Z., Liu Y., Dai Z., Liu W., Zhao K., Zhang T., ... & Dai Y., Synthesis and aromatase inhibitory evaluation of 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives, Bioorg. Med. Chem., 24 (2016) 4723-4730.
- [14] Adhikari N., Amin S. A., Jha T., & Gayen S., Integrating regression and classification-based QSARs with molecular docking analyses to explore the structure-antiaromatase activity relationships of letrozole-based analogs, Can. J. Chem., 95 (2017) 1285-1295.
- [15] Acar Çevik U., Sağlık B. N., Osmaniye D., Levent S., Kaya Çavuşoğlu B., Karaduman A. B., ... & Kaplancıklı Z. A., Synthesis and docking study of benzimidazole–triazolothiadiazine hybrids as aromatase inhibitors, Arch. Pharm., 353 (2020) e2000008.
- [16] Acar Çevik U., Sağlık B.N., Osmaniye D., Levent S., Kaya Çavuşoğlu B., Karaduman A.B., ... & Kaplancıklı Z.A., Synthesis, anticancer evaluation and molecular docking studies of new benzimidazole-1,3,4-oxadiazole derivatives as human topoisomerase types I poison, J. Enzyme Inhib. Med. Chem., 35 (2020) 1657-1673.
Design and Synthesis of Imidazole Derivatives as Anticancer Agents and Potential Aromatase Inhibitors
Abstract
In this study, imidazole derivative compounds were synthesized using the Debus-Radziszewski method. The chemical structures of the compounds were characterized by spectroscopic methods. The effects of target compounds on MCF7 (CRL-3435) were examined and their IC50 values and percent viability were calculated. In addition, the cytotoxic effects on the L929 (CCL-1) normal cell line were evaluated in order to determine the selectivities of the compounds. Then, the inhibition values of aromatase enzyme of the compounds were calculated and compared to the reference compound. When the results were examined, it was observed that Compound la caused the death of breast cancer cells, although not as much as cisplatin, but did not harm healthy cells. In this respect, it was determined that compound Ia has a promising anticancer effect as an aromatase inhibitor.
Keywords
References
- [1] Lekgau K., Raphoko L.A., Lebepe C.M., Mongokoana D.F., Leboho T.C., Matsebatlela T. M., ... & Nxumalo W., Design and Synthesis of 6-Amino-quinoxaline-alkynyl as Potential Aromatase (CYP19A1) Inhibitors, J. Mol. Struct., 1255 (2022) 132473.
- [2] Osmaniye D., Karaca Ş., Kurban B., Baysal M., Ahmad I., Patel H., ... Kaplancıklı Z. A., Design, synthesis, molecular docking and molecular dynamics studies of novel triazolothiadiazine derivatives containing furan or thiophene rings as anticancer agents, Bioorg. Chem., 122 (2022) 105709.
- [3] Sayyad N. B., Sabale P. M., Umare M. D., Bajaj K. K., (2022). Aromatase Inhibitors: Development and Current Perspectives, Indian J. Pharm. Educ. Res.56 (2022) 311-320.
- [4] Shah V., Bhaliya J., Patel G. M., In silico docking and ADME study of deketene curcumin derivatives (DKC) as an aromatase inhibitor or antagonist to the estrogen-alpha positive receptor (Erα+): potent application of breast cancer, Struct. Chem., 33 (2022) 571-600.
- [5] Rashdan H. R., Shehadi I. A., Triazoles Synthesis & Applications as Nonsteroidal Aromatase Inhibitors for Hormone-Dependent Breast Cancer Treatment, Heteroatom Chem., (2022).
- [6] Çevik U. A., Celik I., Mella J., Mellado M., Özkay Y., Kaplancıklı Z. A., Design, Synthesis, and Molecular Modeling Studies of a Novel Benzimidazole as an Aromatase Inhibitor, ACS omega. 7 (2022) 16152-16163.
- [7] Osmaniye D., Levent S., Sağlık B. N., Karaduman A. B., Özkay Y., Kaplancıklı Z. A., Novel imidazole derivatives as potential aromatase and monoamine oxidase-B inhibitors against breast cancer, New J. Chem., 46 (2022) 7442-7451.
- [8] Ammazzalorso A., Gallorini M., Fantacuzzi M., Gambacorta N., De Filippis B., Giampietro L., ... Amoroso R., Design, synthesis and biological evaluation of imidazole and triazole-based carbamates as novel aromatase inhibitors, Eur. J. Med. Chem., 211 (2021) 113115.
- [9] Acar Çevik U., Celik I., Işık A., Ahmad I., Patel H., Özkay Y., & Kaplancıklı Z. A., Design, synthesis, molecular modeling, DFT, ADME and biological evaluation studies of some new 1,3,4-oxadiazole linked benzimidazoles as anticancer agents and aromatase inhibitors, J. Biomol. Struct. Dyn., (2022) 1.
- [10] Ana G., Kelly P. M., Malebari A. M., Noorani S., Nathwani S. M., Twamley B., ... Meegan, M. J., Synthesis and Biological Evaluation of 1 (Diarylmethyl) 1H 1, 2, 4 Triazoles and 1 (Diarylmethyl) 1H Imidazoles as a Novel Class of Anti-Mitotic Agent for Activity in Breast Cancer, Pharma., 14 (2021) 169.
- [11] Asadi P., Khodarahmi G., Farrokhpour H., Hassanzadeh F., Saghaei L., Quantum mechanical/molecular mechanical and docking study of the novel analogues based on hybridization of common pharmacophores as potential anti-breast cancer agents, Res. Pharm. Sci., 12 (2017) 233.
- [12] Mojaddami A., Sakhteman A., Fereidoonnezhad M., Faghih Z., Najdian A., Khabnadideh S., ... Rezaei Z. Binding mode of triazole derivatives as aromatase inhibitors based on docking, protein ligand interaction fingerprinting, and molecular dynamics simulation studies, Res. Pharm. Sci., 12 (2017) 21.
- [13] Song Z., Liu Y., Dai Z., Liu W., Zhao K., Zhang T., ... & Dai Y., Synthesis and aromatase inhibitory evaluation of 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives, Bioorg. Med. Chem., 24 (2016) 4723-4730.
- [14] Adhikari N., Amin S. A., Jha T., & Gayen S., Integrating regression and classification-based QSARs with molecular docking analyses to explore the structure-antiaromatase activity relationships of letrozole-based analogs, Can. J. Chem., 95 (2017) 1285-1295.
- [15] Acar Çevik U., Sağlık B. N., Osmaniye D., Levent S., Kaya Çavuşoğlu B., Karaduman A. B., ... & Kaplancıklı Z. A., Synthesis and docking study of benzimidazole–triazolothiadiazine hybrids as aromatase inhibitors, Arch. Pharm., 353 (2020) e2000008.
- [16] Acar Çevik U., Sağlık B.N., Osmaniye D., Levent S., Kaya Çavuşoğlu B., Karaduman A.B., ... & Kaplancıklı Z.A., Synthesis, anticancer evaluation and molecular docking studies of new benzimidazole-1,3,4-oxadiazole derivatives as human topoisomerase types I poison, J. Enzyme Inhib. Med. Chem., 35 (2020) 1657-1673.
There are 16 citations in total.
Details
| Primary Language | English |
|---|---|
| Subjects | Pharmacology and Pharmaceutical Sciences |
| Journal Section | Natural Sciences |
| Authors | |
| Publication Date | December 27, 2022 |
| Submission Date | June 15, 2022 |
| Acceptance Date | September 28, 2022 |
| Published in Issue | Year 2022 |